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3rd October 2016 @ 22:44

Continuing primary synthesis using small amount of Synthesis of tert-butyl (E)-3-((2-(6-chloropyrazin-2-yl)hydrazono)methyl)piperidine-1-carboxylate (MRLS 3-1) without purification:

compound

MW (g/mol)

mol (mmol) g           density (g/mL) volume (mL) equivalents
MRLS 3-1 339.82 0.294 0.1     1

Diacetoxyiodobenzene

(PhI(OAc)2)

322.10 0.3 0.09663     1
CH2Cl2         3  
MRLS 4-1 337.81  0.294 0.0993     1

Procedure:

Stirred MRLS 3-1 (0.1010g, 0.294 mmol) in 3 mL of CH2Cl2 until completely dissolved. Added PhI(OAc)2 (0.1050 g, 0.3 mmol) and kept stirring the resultant mixture under Argon for 42 hours. 

 

9/17

Checked progress w/ TLC--starting material appeared to be consumed. Removed solvent via rotovap, giving an amber-colored oil. Left in hood overnight.

 

9/18

Purified crude product with flash column chromatography. Used 50% EtOAc in Hexanes as starting eluent, ran gradient up to 100%. 

Collected 28 fractions-- combined fractions 2-4 and rotovapped (yield: 0.0676 g, 68% yield). Left on high-vac overnight. 

 

Took NMR of the combined fractions--(attached on 10/27, sorry for the delay)

Attached Files
1H NMR
13C NMR